Chemistry:Pregnane

Pregnane

Names
IUPAC name 5ξ-Pregnane
Systematic IUPAC name (1S,3aS,3bS,5aΞ,9aS,9bS,11aR)-1-Ethyl-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene
Identifiers
CAS Number	481-26-5 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:8386 Y
ChemSpider	5256760 Y
PubChem CID	6857422
UNII	10Z78HHV4C Y
InChI InChI=1S/C21H36/c1-4-15-9-11-18-17-10-8-16-7-5-6-13-20(16,2)19(17)12-14-21(15,18)3/h15-19H,4-14H2,1-3H3/t15-,16?,17-,18-,19-,20-,21+/m0/s1 Y Key: JWMFYGXQPXQEEM-WZBAXQLOSA-N Y InChI=1/C21H36/c1-4-15-9-11-18-17-10-8-16-7-5-6-13-20(16,2)19(17)12-14-21(15,18)3/h15-19H,4-14H2,1-3H3/t15-,16?,17-,18-,19-,20-,21+/m0/s1 Key: JWMFYGXQPXQEEM-WZBAXQLOBZ
SMILES C41CCCC[C@@]1([C@@H]3[C@H]([C@@H]2CC[C@@H]([C@@]2(C)CC3)CC)CC4)C
Properties
Chemical formula	C21H36
Molar mass	288.511 g/mol
Density	0.926 g/ml
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Pregnane, also known as 17β-ethylandrostane or as 10β,13β-dimethyl-17β-ethylgonane, is a C21 steroid and, indirectly, a parent of progesterone. It is a parent hydrocarbon for two series of steroids stemming from 5α-pregnane (originally allopregnane) and 5β-pregnane (17β-ethyletiocholane). It has a gonane core.

5β-Pregnane is the parent of pregnanediones, pregnanolones, and pregnanediols, and is found largely in urine as a metabolic product of 5β-pregnane compounds.

Pregnanes

Steroid nomenclature: Pregnanes have carbons 1 through 21.

Pregnanes are steroid derivatives with carbons present at positions 1 through 21.

Most biologically significant pregnane derivatives fall into one of two groups: pregnenes and pregnadienes. Another class is pregnatrienes.

Pregnenes

Cortisone

Pregnenes have a double bond. Examples include:

• Cortisone
• Hydrocortisone
• Progesterone

Pregnadienes

Cyproterone acetate

Pregnadienes have two double bonds. Examples include:

• Cyproterone acetate
• Danazol
• Fluocinonide

See also

• 5β-Pregnane
• Pregnanedione
• Pregnanediol
• 19-Norpregnane
• Androstane
• Estrane

External links

• Pregnanes at the US National Library of Medicine Medical Subject Headings (MeSH)
• PubChem
• Diagram at qmul.ac.uk
• Definition of Pregnane
• Progesterone Chemistry
• Progesterone record in European Bioinformatics database